Electrophilic Amination with Nitroarenes

2017 
An exceptionally general electrophilic amination, which directly transforms commercially available nitroarenes with zinc organyls to alkylated aromatic aminoboranes was developed. The reaction starts with a two-step partial reduction of the nitro group to a nitrenoid, which is used in-situ as the electrophilic amination reagent. To facilitate isolation, the resulting air and moisture sensitive aminoboranes were reacted with a range of electrophiles. The protocol not only represents a direct transformation of nitro compounds into an electrophilic amination reagent but also provides an elegant alternative to dehydrocoupling methods for the generation of aminoboranes.
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